Hydrochloric Acid → 2-Bromo-4-iodophenol

Participants

Reaction Conditions

Reaction Steps

Sodium iodide (14.2 g) and sodium hydroxide (3.8 g) were added to a solution of 2-bromophenol (XIX, 16.4 g) in methanol (250 mL). The resultant solution was chilled to 0° C. A commercial bleach solution (6% NaClO, 120 mL) was added drop wise at 0-3° C. over 2 h. After the addition, the reaction mixture was stirred for 1 h at 5° C., then treated with 10% sodium thiosulfate aqueous solution (100 mL) and acidified with concentrated HCl to pH 5-7. The mixture was extracted with EtOAc (150 mL×3). The combined organic layers were partitioned with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The resultant oil was purified by silica gel column chromatography; the product eluted with dichloromethane/hexane (2:3), to afford the desired product as a colorless solid (14.76 g, 52%).

Provenance & Evidence